4-Ethyl-3-(3-pyrid-yl)-1H-1,2,4-triazole-5(4H)-thione 0.095-hydrate.

The title compound, C(9)H(10)N(4)S·0.095H(2)O, consists of discrete 4-ethyl-3-(3-pyrid-yl)-1H-1,2,4-triazole-5(4H)-thione mol-ecules and a disordered mol-ecule of water of hydration with partial occupancy, lying on a twofold rotation axis. The dihedral angle between the pyridine and triazole rings is 41.73 (8)°. In the crystal structure, mol-ecules are hydrogen bonded via triazole NH groups and pyridyl N atoms, forming chains parallel to the a axis.

Related literature

For related literature, see: Ahmad et al. (2001 ▶); Chai et al. (2003 ▶); Dege et al. (2004 ▶, 2005 ▶)); Demir et al. (2006 ▶); Dobosz et al. (2003 ▶); Hashimoto et al. (1990 ▶); Kanazawa et al. (1988 ▶); Mazur et al. (2006 ▶).

Experimental

Crystal data

C9H10N4S·0.095H2O

M = 207.96

Monoclinic,

a = 14.076 (5) Å

b = 8.877 (5) Å

c = 16.216 (8) Å

β = 93.25 (3)°

V = 2023.0 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 173 (2) K

0.18 × 0.16 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.950, T max = 0.972

3392 measured reflections

2297 independent reflections

1616 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.107

S = 1.05

2297 reflections

137 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.25 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011744/lh2615sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011744/lh2615Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H10N4S·0.095H2O	F000 = 872
Mr = 207.96	Dx = 1.366 Mg m−3
Monoclinic, C2/c	Melting point = 440–441 K
Hall symbol: -C 2yc	Mo Kα radiation λ = 0.71073 Å
a = 14.076 (5) Å	Cell parameters from 3392 reflections
b = 8.877 (5) Å	θ = 3.6–27.4º
c = 16.216 (8) Å	µ = 0.29 mm−1
β = 93.25 (3)º	T = 173 (2) K
V = 2023.0 (17) Å3	Block, colorless
Z = 8	0.18 × 0.16 × 0.10 mm

Nonius KappaCCD diffractometer	2297 independent reflections
Radiation source: fine-focus sealed tube	1616 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
T = 173(2) K	θmax = 27.4º
ω and φ scans	θmin = 3.6º
Absorption correction: Multi-scan(SORTAV; Blessing, 1997)	h = −17→18
Tmin = 0.950, Tmax = 0.972	k = −11→9
3392 measured reflections	l = −20→20

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.042	w = 1/[σ2(Fo2) + (0.0405P)2 + 1.636P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.107	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.24 e Å−3
2297 reflections	Δρmin = −0.25 e Å−3
137 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0038 (9)
Secondary atom site location: difference Fourier map

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	−0.12974 (4)	0.05644 (7)	−0.11164 (3)	0.0415 (2)
O1	0.0000	−0.0319 (16)	−0.2500	0.070 (4)	0.19
N1	−0.07296 (10)	0.26787 (18)	0.09536 (9)	0.0256 (4)
N2	−0.13013 (11)	0.19176 (19)	0.03795 (10)	0.0276 (4)
H2	−0.1854 (16)	0.158 (3)	0.0530 (12)	0.033*
N3	0.00251 (10)	0.22103 (18)	−0.01818 (9)	0.0228 (4)
N4	0.21945 (11)	0.53359 (19)	0.10227 (10)	0.0290 (4)
C1	0.00713 (12)	0.2838 (2)	0.05951 (10)	0.0217 (4)
C2	−0.08639 (13)	0.1576 (2)	−0.03071 (12)	0.0267 (4)
C3	0.14695 (12)	0.4604 (2)	0.06268 (11)	0.0246 (4)
H3	0.1343	0.4794	0.0055	0.029*
C4	0.08963 (12)	0.3582 (2)	0.10142 (11)	0.0220 (4)
C5	0.10899 (13)	0.3310 (2)	0.18541 (11)	0.0263 (4)
H5	0.0714	0.2616	0.2140	0.032*
C6	0.18343 (14)	0.4061 (2)	0.22654 (12)	0.0313 (5)
H6	0.1977	0.3897	0.2838	0.038*
C7	0.23642 (13)	0.5050 (2)	0.18282 (12)	0.0313 (5)
H7	0.2878	0.5559	0.2113	0.038*
C8	0.07912 (14)	0.1998 (2)	−0.07478 (12)	0.0300 (5)
H8A	0.0756	0.0962	−0.0973	0.036*
H8B	0.1412	0.2110	−0.0436	0.036*
C9	0.07367 (17)	0.3113 (3)	−0.14570 (13)	0.0406 (6)
H9A	0.1216	0.2857	−0.1849	0.049*
H9B	0.0856	0.4132	−0.1243	0.049*
H9C	0.0102	0.3072	−0.1738	0.049*

	U11	U22	U33	U12	U13	U23
S1	0.0476 (4)	0.0346 (4)	0.0398 (3)	−0.0034 (3)	−0.0202 (3)	−0.0060 (2)
O1	0.107 (12)	0.043 (9)	0.063 (9)	0.000	0.034 (9)	0.000
N1	0.0194 (8)	0.0271 (10)	0.0300 (8)	−0.0060 (7)	−0.0022 (6)	0.0005 (7)
N2	0.0201 (8)	0.0283 (10)	0.0339 (9)	−0.0080 (7)	−0.0032 (7)	0.0017 (7)
N3	0.0228 (8)	0.0221 (9)	0.0232 (8)	−0.0008 (7)	−0.0026 (6)	0.0016 (6)
N4	0.0220 (8)	0.0282 (10)	0.0367 (9)	−0.0042 (7)	0.0002 (7)	0.0000 (7)
C1	0.0209 (9)	0.0215 (10)	0.0225 (9)	−0.0007 (8)	−0.0008 (7)	0.0031 (7)
C2	0.0256 (10)	0.0221 (11)	0.0315 (10)	−0.0015 (8)	−0.0076 (8)	0.0044 (8)
C3	0.0199 (9)	0.0269 (11)	0.0267 (9)	−0.0012 (8)	−0.0001 (7)	0.0024 (8)
C4	0.0180 (9)	0.0212 (10)	0.0267 (9)	−0.0001 (7)	0.0005 (7)	−0.0007 (8)
C5	0.0234 (10)	0.0288 (11)	0.0268 (9)	−0.0024 (8)	0.0027 (7)	−0.0005 (8)
C6	0.0298 (10)	0.0399 (13)	0.0237 (9)	−0.0020 (9)	−0.0034 (8)	−0.0027 (9)
C7	0.0226 (10)	0.0333 (12)	0.0373 (11)	−0.0047 (9)	−0.0052 (8)	−0.0081 (9)
C8	0.0316 (10)	0.0289 (12)	0.0299 (10)	0.0029 (9)	0.0044 (8)	−0.0006 (9)
C9	0.0540 (14)	0.0397 (14)	0.0289 (11)	0.0010 (11)	0.0096 (10)	0.0024 (10)

S1—C2	1.676 (2)	C3—C4	1.388 (3)
S1—O1	3.074 (4)	C3—H3	0.9500
O1—S1i	3.074 (4)	C4—C5	1.395 (3)
O1—N1ii	3.382 (9)	C5—C6	1.381 (3)
N1—C1	1.305 (2)	C5—H5	0.9500
N1—N2	1.373 (2)	C6—C7	1.375 (3)
N2—C2	1.337 (3)	C6—H6	0.9500
N2—H2	0.88 (2)	C7—H7	0.9500
N3—C1	1.376 (2)	C8—C9	1.516 (3)
N3—C2	1.377 (2)	C8—H8A	0.9900
N3—C8	1.467 (2)	C8—H8B	0.9900
N4—C7	1.339 (3)	C9—H9A	0.9800
N4—C3	1.342 (2)	C9—H9B	0.9800
C1—C4	1.469 (2)	C9—H9C	0.9800
C2—S1—O1	120.21 (15)	C5—C4—C1	118.66 (16)
S1—O1—S1i	150.4 (5)	C6—C5—C4	119.26 (18)
S1—O1—N1ii	77.57 (10)	C6—C5—H5	120.4
S1i—O1—N1ii	122.08 (18)	C4—C5—H5	120.4
C1—N1—N2	103.82 (16)	C7—C6—C5	118.57 (18)
C2—N2—N1	113.35 (16)	C7—C6—H6	120.7
C2—N2—H2	127.4 (14)	C5—C6—H6	120.7
N1—N2—H2	118.2 (14)	N4—C7—C6	123.51 (17)
C1—N3—C2	107.22 (15)	N4—C7—H7	118.2
C1—N3—C8	128.79 (15)	C6—C7—H7	118.2
C2—N3—C8	123.33 (16)	N3—C8—C9	112.54 (17)
C7—N4—C3	117.62 (17)	N3—C8—H8A	109.1
N1—C1—N3	111.53 (16)	C9—C8—H8A	109.1
N1—C1—C4	121.52 (16)	N3—C8—H8B	109.1
N3—C1—C4	126.94 (16)	C9—C8—H8B	109.1
N2—C2—N3	104.00 (16)	H8A—C8—H8B	107.8
N2—C2—S1	127.52 (15)	C8—C9—H9A	109.5
N3—C2—S1	128.46 (16)	C8—C9—H9B	109.5
N4—C3—C4	123.08 (17)	H9A—C9—H9B	109.5
N4—C3—H3	118.5	C8—C9—H9C	109.5
C4—C3—H3	118.5	H9A—C9—H9C	109.5
C3—C4—C5	117.95 (16)	H9B—C9—H9C	109.5
C3—C4—C1	123.31 (16)
C2—S1—O1—S1i	−60.83 (15)	O1—S1—C2—N3	5.5 (3)
C2—S1—O1—N1ii	74.7 (3)	C7—N4—C3—C4	0.2 (3)
C1—N1—N2—C2	1.6 (2)	N4—C3—C4—C5	−0.1 (3)
N2—N1—C1—N3	0.1 (2)	N4—C3—C4—C1	176.65 (18)
N2—N1—C1—C4	−178.76 (16)	N1—C1—C4—C3	−137.4 (2)
C2—N3—C1—N1	−1.8 (2)	N3—C1—C4—C3	43.9 (3)
C8—N3—C1—N1	−172.57 (17)	N1—C1—C4—C5	39.3 (3)
C2—N3—C1—C4	177.06 (18)	N3—C1—C4—C5	−139.4 (2)
C8—N3—C1—C4	6.3 (3)	C3—C4—C5—C6	0.2 (3)
N1—N2—C2—N3	−2.7 (2)	C1—C4—C5—C6	−176.73 (18)
N1—N2—C2—S1	175.75 (14)	C4—C5—C6—C7	−0.3 (3)
C1—N3—C2—N2	2.6 (2)	C3—N4—C7—C6	−0.4 (3)
C8—N3—C2—N2	174.01 (16)	C5—C6—C7—N4	0.4 (3)
C1—N3—C2—S1	−175.82 (15)	C1—N3—C8—C9	−105.1 (2)
C8—N3—C2—S1	−4.4 (3)	C2—N3—C8—C9	85.4 (2)
O1—S1—C2—N2	−172.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N4iii	0.88 (2)	1.94 (2)	2.792 (3)	162 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N4i	0.88 (2)	1.94 (2)	2.792 (3)	162 (2)

Symmetry code: (i) .